Synthesis and biological evaluation of derivatives of 2-{2-fluoro-4-[(2- oxocyclopentyl)methyl]phenyl}propanoic acid: Nonsteroidal anti-inflammatory drugs with low gastric ulcerogenic activity

Naoki Yamakawa, Shintaro Suemasu, Yoshinari Okamoto, Ken Ichiro Tanaka, Tomoaki Ishihara, Teita Asano, Keishi Miyata, Masami Otsuka, Tohru Mizushima

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

We previously reported that 2-fluoroloxoprofen has lower gastric ulcerogenic activity than loxoprofen, a nonsteroidal anti-inflammatory drug (NSAID) without selectivity for COX-2. We synthesized derivatives of 2-fluoroloxoprofen and studied their properties. Compared to 2-fluoroloxoprofen, one derivative, 11a, exhibited higher anti-inflammatory activity and an equivalent ulcerogenic effect. These results suggest that 11a could be therapeutically beneficial for use as an NSAID.

Original languageEnglish
Pages (from-to)5143-5150
Number of pages8
JournalJournal of Medicinal Chemistry
Volume55
Issue number11
DOIs
Publication statusPublished - 2012 Jun 14

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Stomach
Anti-Inflammatory Agents
Pharmaceutical Preparations
propionic acid
loxoprofen

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery

Cite this

Synthesis and biological evaluation of derivatives of 2-{2-fluoro-4-[(2- oxocyclopentyl)methyl]phenyl}propanoic acid : Nonsteroidal anti-inflammatory drugs with low gastric ulcerogenic activity. / Yamakawa, Naoki; Suemasu, Shintaro; Okamoto, Yoshinari; Tanaka, Ken Ichiro; Ishihara, Tomoaki; Asano, Teita; Miyata, Keishi; Otsuka, Masami; Mizushima, Tohru.

In: Journal of Medicinal Chemistry, Vol. 55, No. 11, 14.06.2012, p. 5143-5150.

Research output: Contribution to journalArticle

Yamakawa, Naoki ; Suemasu, Shintaro ; Okamoto, Yoshinari ; Tanaka, Ken Ichiro ; Ishihara, Tomoaki ; Asano, Teita ; Miyata, Keishi ; Otsuka, Masami ; Mizushima, Tohru. / Synthesis and biological evaluation of derivatives of 2-{2-fluoro-4-[(2- oxocyclopentyl)methyl]phenyl}propanoic acid : Nonsteroidal anti-inflammatory drugs with low gastric ulcerogenic activity. In: Journal of Medicinal Chemistry. 2012 ; Vol. 55, No. 11. pp. 5143-5150.
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